I need to organize rent collection next week.  

If you are just trying to get going and focused on Chicago make sure to check out @Mark Ainley 's Chicago investor focused podcast:  https://www.straightupchicagoi...The one thing I've always found about mentors is that they have come organically. 

Here are thee tools I use:IGMS for communication with guests and automation of communication (free for 1 property)PriceLabs for organizing min stays on what days and for far out bookings as well as dynamic pricing ($20/ mo)Remote lock for my automated keyless entry front door ($6/ mo).

One of my biggest worries is that I'll spend too much time and effort on bookkeeping and organization.

Gothca and you have the ability to really scope out what your bidding on so that if it does not redeem your happy to own it correct.when i went to tax lien Auctions in MS  it moved so fast there was no way to know what the heck you were bidding on.. of course you had the highly organized groups with 3 kids and their lap tops.. and the auctioneer would favor the known locals.. this was Hinds and Rankin counties.   

Going with a licensed agent is suggested, as well as going with someone who is a member of a property management based organization such as NARPM (National Association of Residential Property Managers) or is certified as a property manager within their state.

I would like to know how to setup my business and organize my properties so1. 

Are you talking about having a website to capture leads and driving traffic to that site via organic and paid search?

They also offer background checks/credit checks and its all saved to your rent prep profile which makes it easy to organize. 

She is super responsive and organized.